The present invention pertains to a new process for oxidizing olefins.
Olefins have been oxidized to form oxirane compounds by various methods such as by the dehydrochlorination of chlorohydrins, (P. P. McClellan, Ind. Eng. Chem., Vol. 42, 12 (1950), pp. 2402-7) the reaction of hydroperoxides with olefins in the presence of catalysts (U.S. 3,351,635 and R. Landau, et al., Seventh World Petroleum Conference Proceedings, Vol. 5, (1967), pp. 67-72) and uniquely, ethylene can be converted to ethylene oxide by the direct vapor phase oxidation of ethylene with air or oxygen in the presence of a silver catalyst. Olefins have also been oxidized to form oxirane compounds by treatment with organic peracids such as peracetic acid, monoperphthalic acid and perbenzoic acid (U.S. Pat. No. 3,341,556 and Chem. Revs. Vol. 45, (1949) pp. 16-25).
The present invention therefor provides an alternate method for the preparation of oxirane compounds from compounds containing olefinic unsaturation, said method having the following characteristics:
1. A relatively high selectivity to the oxirane product, PA1 2. a minimum of non-useful by-products, PA1 3. no organic co-product, PA1 4. versatility in that various olefins can be epoxidized by the process of the present invention, PA1 5. the process can be conducted where the periodate is in the liquid or solid state, PA1 6. the separation of the oxirane compounds from the periodate is relatively easy, especially when the periodate is a solid. PA1 (I)--MIO.sub.4, PA1 (ii)--mh.sub.4 io.sub.6, or PA1 (III)--M.sub.2 H.sub.3 IO.sub.6